Textbook-Integrated Guide to Educational Resources

TIGER

Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig ReactionEric Martin and Cynthia Kellen-YuenA microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ.2007, 84, 2004.

Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory ExperimentSam H. Leung and Stephen A. AngelIn this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.Leung, Sam H.; Angel, Stephen A. J. Chem. Educ.2004, 81, 1492.

A source of isomer-drawing assignmentsKjonaas, Richard A.A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.Kjonaas, Richard A. J. Chem. Educ.1992, 69, 452.

The scope of the Haworth synthesisAgranat, Israel; Shih, Yu-ShanThe duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.Agranat, Israel; Shih, Yu-Shan J. Chem. Educ.1976, 53, 488.

Illustrating gas chromatography and mass spectrometry. An undergraduate experimentGross, Michael L.; Olsen, Virgil K.; Forc, R. KenOne lab period is used to separate and collect the components of a ketone mixture; the second lab period is used to explain and demonstrate the MS instrumentation and the interpretation of ketone spectra; and in part three the spectra of the separated ketones are analyzed by individual students.Gross, Michael L.; Olsen, Virgil K.; Forc, R. Ken J. Chem. Educ.1975, 52, 535.